6-Methyl-5-nitro-2,4(1H,3H)-pyrimidinedione

Light Yellow Crystalline Solid

The procedure was adapted from that reported in J. Med. Chem. 1976, 19, 1072. 6-Methylpyrimidine-2, 4(lH, 3H)-dione (7.Og, 55.56mmol) was added to concentrated sulfuric acid (26 mL) cooled in ice at such a rate that the internal The raw material 11 (6.3g) was dissolved in 30ml concentrated sulfuric acid and slowly mixed with low acid (concentrated sulfuric acid / concentrated nitric acid = 10ml / 12ml) at -2 . Finally, the reaction was carried out at 35 for 12h.The reaction solution was poured into ice water and precipitated with a large amount of a pale yellow solid. After filtration under reduced pressure, a pale yellow solid 12 (4 g) was obtained in a yield of 65.2percent.To a stirred mixture of 96percent HThe procedure was adapted from that reported in J. Med. Chem. 1976, 19, 1072. 6-Methylpyrimidine-2, 4(lH, 3H)-dione (7.Og, 55.56mmol) was added to concentrated sulfuric acid (26 mL) cooled in ice at such a rate that the internal Parent compound 5 was synthesized starting from commercially available 6-methyluracil (1), shown in Scheme 1. Nitration at C5 was accomplished by adding 6-methyluracil to a solution ofconcentrated sulfuric and nitric acids at 0 C, followed by quenching in ice water to give 2 as apale yellow solid [24]. This was followed by a modified Batcho-Leimgruber indole synthesis tofirst prepare enamine 3 [52, 53]. Ring cyclization is accomplished by reduction of the nitro moietyto an amino group, with subsequent nucleophilic attack at C8 by the amino lone pair with loss of dimethylamine. The reduction of the nitro group is accomplished by stirring 3 in acetic acid and zincdust overnight at 80 C, followed by filtration, formation of the N5 sodium salt via NaOH dissolution, then re-acidification and collection of solid 4 [23, 24]The raw material 11 (6.3g) was dissolved in 30ml concentrated sulfuric acid and slowly mixed with low acid (concentrated sulfuric acid / concentrated nitric acid = 10ml / 12ml) at -2 . Finally, the reaction was carried out at 35 for 12h.The reaction solution was poured into ice water and precipitated with a large amount of a pale yellow solid. After filtration under reduced pressure, a pale yellow solid 12 (4 g) was obtained in a yield of 65.2%.a) 50.5 g (0.40 mol) of 6-methyluracil (Merck) are introduced in portions over the course of one hour with stirring at 0 to +5 C. into a solution of 200 ml of 100% nitric acid (fuming) and 50 g of phosphorus pentoxide. When the exothermic reaction is complete, the mixture is stirred at +5 C. for a further 5 hours. The reaction mixture is subsequently poured into 1 kg of ice-water. The resultant precipitate is filtered, washed with water and then dried to constant weight, giving 37 g (54%) of In a 100 mL eggplant flask was added 520 ml of concentrated sulfuric acid, Under ice bath, 140 g of 6-methyluracil was added in portions, Keep the temperature no more than 40 C. After all dissolved, Slowly dropping 104ml fuming nitric acid, keep the temperature does not exceed 15 .Drop finished, After stirring at room temperature for 30 min, The reaction solution was poured into crushed ice, Have a solid wash out. Filter, filter cake by water, Acetone was washed and dried to give the title compound 1-1.To a stirred mixture of 96% H2S04(15 mL) and of 70% HN03(15 mL) was added 6- methyl pyrimidine-2, 4-(lH, 3H)-dione (2.5 g, 19.8 mmol). The solution was kept at 50 C for lOh. The mixture was cooled to room temperature and poured into a large volume of ice water. The solid was collected and dried in vacuo. Recrystallization with MeOH gave the final compound (2.7g, 16.2 mmol) as yellows solid.1H NMR (200 MHz, DMSO) delta 2.31 (s, 3H), 11.82 (s, 1H), 11.85 (s, 1H).

A synthetic intermediate

Molecular Weight:171.11
XLogP3:-0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Exact Mass:171.02800565
Monoisotopic Mass:171.02800565
Topological Polar Surface Area:104
Heavy Atom Count:12
Complexity:300
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes